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I'm an life section copy editor, designer and occasional writer at a midsize daily in the upper Midwest that loves to pat itself on the back for its achievements.

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I'm trying to land a job in Chicago because my girlfriend is moving there for grad school. I doubt that any hiring editor outside of my state would know this paper when I apply for jobs.

Do you have any advice for selling myself in a cover letter without coming off as bragging or even delusional for trying to make the jump?

I've redesigned the entertainment tabloid, attended the weeklong typography seminar at Poynter, speak Spanish pretty well and have recently had a small piece published in Esquire. I like to tout myself in a cover letter, but how much is too much? Four paragraphs?

And how important is a witty lede? Sometimes, I wonder if my sense of humor might get my resume relegated to the paper shredder.

Thanks,

Chicago Bound

Who could answer your question better than Sheila Solomon, who recruits for the Chicago Tribune. I asked her to answer your question, and she kindly agreed.

-- Joe

Experience from a midsize daily can be an ideal path to a metropolitan daily and in fact is the path most taken.

As you prepare for your move, I'd first identify the many dailies in the Chicago area and check for any job postings. At the same time, I'd find out who recruits for those newsrooms and send a brief cover letter, resume and work samples to that person. Follow up in about a week with an e-mail and/or phone call to see if you sent enough materials and if they've received them.

The letter should be clear about the job you're seeking, concentrating either on your strengths (years of experience, foreign language expertise, etc.) or your desire to develop other interests. For example, I can't tell whether you want to continue as a copy editor/page designer or pursue a reporting position, though I'm guessing you have more experience as an editor.

If responding to a specific job, be clear about your skills for it and follow the directions of the posting. Don't sell yourself short in the cover letter or in any other mode of communication because you think your paper's too small to be recognized by the big metros.

The letter should also tell editors when you're planning to make the move or will be available for interviews and include a daytime phone number that has voicemail.
-- Sheila Solomon